Dolabelladienols A–C, New Diterpenes Isolated from Brazilian Brown Alga Dictyota pfaffii
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2014 |
| Outros Autores: | , , , , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da FIOCRUZ (ARCA) |
| DOI: | 10.3390/md12074247 |
| Texto Completo: | https://www.arca.fiocruz.br/handle/icict/11930 |
Resumo: | Universidad Nacional de Colombia. Departamento de Química. Bogotá, D.C, Colombia. |
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Pardo-Vargas, AlonsoOliveira, Ingrid de BarcelosStephens, Paulo Roberto SoaresSantos, Claudio Cesar CirnePaixão, Izabel Christina Nunes de PalmerRamos, Freddy AlejandroJiménez, CarlosRodriguez, JaimeResende, Jackson Antonio Lamounier CamargosTeixeira, Valeria LaneuvilleCastellanos, Leonardo2015-10-12T16:25:07Z2015-10-12T16:25:07Z2014PARDO-VARGAS, Alonso; et al. Dolabelladienols A–C, New Diterpenes Isolated from Brazilian Brown Alga Dictyota pfaffii. Mar. Drugs, v.12, p.4247-4259, 2014.1660-3397https://www.arca.fiocruz.br/handle/icict/1193010.3390/md12074247engMDPIDolabelladienols A–C, New Diterpenes Isolated from Brazilian Brown Alga Dictyota pfaffiiinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleUniversidad Nacional de Colombia. Departamento de Química. Bogotá, D.C, Colombia.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Imunologia Clínica. Rio de Janeiro, RJ, Brasil / Universidade Federal Fluminense. Instituto de Biologia. Departamento de Biologia Celular e Molecular. Programa de Pós-graduação em Ciências e Biotecnologia. Laboratório de Virologia Molecular e Biotecnologia Marinha. Niterói, RJ, Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Imunologia Clínica. Rio de Janeiro, RJ, Brasil / Universidade Federal Fluminense. Instituto de Biologia. Departamento de Biologia Celular e Molecular. Programa de Pós-graduação em Ciências e Biotecnologia. Laboratório de Virologia Molecular e Biotecnologia Marinha. Niterói, RJ, Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Imunologia Clínica. Rio de Janeiro, RJ, Brasil / Universidade Federal Fluminense. Instituto de Biologia. Departamento de Biologia Celular e Molecular. Programa de Pós-graduação em Ciências e Biotecnologia. Laboratório de Virologia Molecular e Biotecnologia Marinha. Niterói, RJ, Brasil.Universidade Federal Fluminense. Instituto de Biologia. Departamento de Biologia Celular e Molecular. Programa de Pós-graduação em Ciências e Biotecnologia. Laboratório de Virologia Molecular e Biotecnologia Marinha. Niterói, RJ, Brasil.Universidad Nacional de Colombia. Departamento de Química. Bogotá, D.C, Colombia.Universidade da Coruña. Facultade de Ciencias and Centro de Investigaciones Científicas Avanzadas (CICA). Departamento de Química Fundamental. Coruña, Spain.Universidade da Coruña. Facultade de Ciencias and Centro de Investigaciones Científicas Avanzadas (CICA). Departamento de Química Fundamental. Coruña, Spain.Universidade Federal Fluminense. Instituto de Química. Laboratório de Difração de Raios X. Niterói, RJ, Brasil.Universidad Nacional de Colombia. Departamento de Química. Bogotá, D.C, Colombia.The marine brown alga Dictyota pfaffii from Atol das Rocas, in Northeast Brazil is a rich source of dolabellane diterpene, which has the potential to be used in future antiviral drugs by inhibiting reverse transcriptase (RT) of HIV-1. Reexamination of the minor diterpene constituents yielded three new dolabellane diterpenes, (1R*,2E,4R*,7S,10S*,11S*,12R*)10,18-diacetoxy-7-hydroxy-2,8(17)-dolabelladiene (1), (1R*,2E,4R*,7R*,10S*,11S*,12R*)10,18-diacetoxy-7-hydroxy-2,8(17)-dolabelladiene (2), (1R*,2E,4R*,8E,10S*,11S,12R*)10,18-diacetoxy-7-hydroxy-2,8-dolabelladiene (3), termed dolabelladienols A–C (1–3) respectively, in addition to the known dolabellane diterpenes (4–6). The elucidation of the compounds 1–3 was assigned by 1D and 2D NMR, MS, optical rotation and molecular modeling, along with the relative configuration of compound 4 and the absolute configuration of 5 by X-ray diffraction. The potent anti-HIV-1 activities displayed by compounds 1 and 2 (IC50 = 2.9 and 4.1 μM), which were more active than even the known dolabelladienetriol 4, and the low cytotoxic activity against MT-2 lymphocyte tumor cells indicated that these compounds are promising anti-HIV-1 agents.Marine natural productsDictyota pfaffiiDolabellane diterpenesAnti-HIV-1HIV-1info:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txtlicense.txttext/plain; charset=utf-82354https://www.arca.fiocruz.br/bitstream/icict/11930/1/license.txt8b4c200b4e10021c5683c6ccaba07169MD51ORIGINALingrid_oliveira_etal_IOC_2014.pdfingrid_oliveira_etal_IOC_2014.pdfapplication/pdf775833https://www.arca.fiocruz.br/bitstream/icict/11930/2/ingrid_oliveira_etal_IOC_2014.pdfaa8c2188595e6e23695afe7672a67d35MD52TEXTingrid_oliveira_etal_IOC_2014.pdf.txtingrid_oliveira_etal_IOC_2014.pdf.txtExtracted texttext/plain36881https://www.arca.fiocruz.br/bitstream/icict/11930/3/ingrid_oliveira_etal_IOC_2014.pdf.txtbc41be088f0ec541be1fefc08d96015dMD53icict/119302023-09-05 10:36:35.584oai:www.arca.fiocruz.br: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Repositório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352023-09-05T13:36:35Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false |
| dc.title.pt_BR.fl_str_mv |
Dolabelladienols A–C, New Diterpenes Isolated from Brazilian Brown Alga Dictyota pfaffii |
| title |
Dolabelladienols A–C, New Diterpenes Isolated from Brazilian Brown Alga Dictyota pfaffii |
| spellingShingle |
Dolabelladienols A–C, New Diterpenes Isolated from Brazilian Brown Alga Dictyota pfaffii Pardo-Vargas, Alonso Marine natural products Dictyota pfaffii Dolabellane diterpenes Anti-HIV-1 HIV-1 |
| title_short |
Dolabelladienols A–C, New Diterpenes Isolated from Brazilian Brown Alga Dictyota pfaffii |
| title_full |
Dolabelladienols A–C, New Diterpenes Isolated from Brazilian Brown Alga Dictyota pfaffii |
| title_fullStr |
Dolabelladienols A–C, New Diterpenes Isolated from Brazilian Brown Alga Dictyota pfaffii |
| title_full_unstemmed |
Dolabelladienols A–C, New Diterpenes Isolated from Brazilian Brown Alga Dictyota pfaffii |
| title_sort |
Dolabelladienols A–C, New Diterpenes Isolated from Brazilian Brown Alga Dictyota pfaffii |
| author |
Pardo-Vargas, Alonso |
| author_facet |
Pardo-Vargas, Alonso Oliveira, Ingrid de Barcelos Stephens, Paulo Roberto Soares Santos, Claudio Cesar Cirne Paixão, Izabel Christina Nunes de Palmer Ramos, Freddy Alejandro Jiménez, Carlos Rodriguez, Jaime Resende, Jackson Antonio Lamounier Camargos Teixeira, Valeria Laneuville Castellanos, Leonardo |
| author_role |
author |
| author2 |
Oliveira, Ingrid de Barcelos Stephens, Paulo Roberto Soares Santos, Claudio Cesar Cirne Paixão, Izabel Christina Nunes de Palmer Ramos, Freddy Alejandro Jiménez, Carlos Rodriguez, Jaime Resende, Jackson Antonio Lamounier Camargos Teixeira, Valeria Laneuville Castellanos, Leonardo |
| author2_role |
author author author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Pardo-Vargas, Alonso Oliveira, Ingrid de Barcelos Stephens, Paulo Roberto Soares Santos, Claudio Cesar Cirne Paixão, Izabel Christina Nunes de Palmer Ramos, Freddy Alejandro Jiménez, Carlos Rodriguez, Jaime Resende, Jackson Antonio Lamounier Camargos Teixeira, Valeria Laneuville Castellanos, Leonardo |
| dc.subject.en.pt_BR.fl_str_mv |
Marine natural products Dictyota pfaffii Dolabellane diterpenes Anti-HIV-1 |
| topic |
Marine natural products Dictyota pfaffii Dolabellane diterpenes Anti-HIV-1 HIV-1 |
| dc.subject.decs.pt_BR.fl_str_mv |
HIV-1 |
| description |
Universidad Nacional de Colombia. Departamento de Química. Bogotá, D.C, Colombia. |
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2014 |
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2014 |
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2015-10-12T16:25:07Z |
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2015-10-12T16:25:07Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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article |
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publishedVersion |
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PARDO-VARGAS, Alonso; et al. Dolabelladienols A–C, New Diterpenes Isolated from Brazilian Brown Alga Dictyota pfaffii. Mar. Drugs, v.12, p.4247-4259, 2014. |
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https://www.arca.fiocruz.br/handle/icict/11930 |
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1660-3397 |
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10.3390/md12074247 |
| identifier_str_mv |
PARDO-VARGAS, Alonso; et al. Dolabelladienols A–C, New Diterpenes Isolated from Brazilian Brown Alga Dictyota pfaffii. Mar. Drugs, v.12, p.4247-4259, 2014. 1660-3397 10.3390/md12074247 |
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